As a player, Paul Ince won two Premiership titles, two FA Cup winners' medals and a European Cup Winners' Cup medal, as well as 53 England caps.
Ince is finding being a manager is a big challenge
But now, as manager of the League's bottom side Macclesfield Town, he faces possibly his biggest challenge yet.
"Taking this club forward is going to take time, and we have a long-term plan," he told BBC Sport.
"If I'd been here at the start of the season, with the players we've got, I think we'd be in the top three."
Self-styled 'Guv'nor' Ince took charge of Macclesfield in October, following the sacking of Brian Horton.
Despite an FA Cup first round replay win over Walsall, he is still awaiting his first League win.
And with the club ten points adrift of second-from-bottom Boston, admitted his new job was throwing up new challenges.
"Being a manager is hard work, and it can be a lonely job. Especially if things aren't going well," he said.
If it wasn't for John Lyall I wouldn't be where I am today
Ince says it was important to "get the lads laughing again" in training, and a recent visit by former England team-mate Ian Wright is sure to have lifted spirits.
As well as playing alongside some of the game's biggest names, Ince played under some of
football's most successful managers.
And he has taken a selection of their ideas and attitudes to formulate his own management style, rather than just follow one example.
The face says it all: Ince feels the strain of management
"Inevitably I learned a lot from him and all the managers I played under," he said.
"Sir Alex Ferguson is a great motivator and sets high standards. Glenn Hoddle is very meticulous and thorough in his work.
"Terry Venables simplified things, he never overloaded you but would say the right one or two things that would improve each individual."
But it was the late John Lyall, his mentor in his early days at West Ham, for whom Ince has the most affection.
"He was my greatest influence - he was the manager who made me the player that I was," he said.
"He was like a father figure to me - hard but fair. If it wasn't for him I wouldn't be where I am today."
Where he is today is at the bottom of the footballing heap.
Never one to shirk a challenge, Ince is relishing the job in hand, but realises his past achievements will not help drag Macclesfield up the table.
"It's a tough ask," he said.
"Anyone going into management who played at a high level commands immediate respect but that doesn't last long.
"You have to earn respect for what you do as a manager, not what you did as a player. I know I'm just learning my trade.
If I can be as successful as a manager as I was as a player, I'll be more than happy
"We must concentrate on the short-term and that is staying in this division.
"On the pitch we have started to cut out the silly mistakes, work as a unit and build from there."
Ince is not short of confidence or ambition - for the team or himself.
"I'm on the first rung of the ladder and want to do as well as I can with Macclesfield - and personally, I want to do as well as I can, too.
"That means at some point in the future possibly managing in the Premiership or even managing England.
"I am one of the lucky ones - I played for big clubs here and abroad and played for my country, I played alongside great players and I won trophies - I'll never look back and wish it had been different.
"Management is a new path for me and if I can be as successful there as I was as a player, I'll be more than happy."